Medicare 2026

Big Employer or Small? The Rule That Decides Medicare at 65

HARTFORD, Conn. — More people in and around Hartford are staying on the job past 65, and that raises a fair question: do you have to take Medicare when you're still covered at work? The short answer is that it depends on the size of your employer — and getting that one detail right can save you from a lifelong late penalty.

The rule that changes everything: employer size

Medicare uses something called "coordination of benefits" to decide which insurance pays first when you have both. The dividing line is 20 employees.

• 20 or more employees: Your group health plan is the "primary" payer. Medicare is secondary. Many people in this situation delay Part B (which has a monthly premium) and keep their employer plan.
• Fewer than 20 employees: Medicare is usually primary. In this case, you generally need to enroll in Part A and Part B at 65, because your employer plan expects Medicare to pay first. If you skip Part B, you could end up with big bills the employer plan won't cover.

If you're not sure how your employer's plan is set up, ask your HR or benefits office directly. This is one question worth putting in writing.

Part A is usually a yes

Part A covers hospital stays and, for most people, has no monthly premium because they or a spouse paid Medicare taxes while working. Many people sign up for Part A at 65 even if they keep employer coverage.

One important exception: if you contribute to a Health Savings Account (HSA), you cannot keep adding to it once you enroll in any part of Medicare, including Part A. If your HSA matters to you, talk with your benefits team before you enroll.

Part B: delay it or take it?

Part B covers doctor visits and outpatient care, and it comes with a monthly premium. Whether to delay Part B depends on that 20-employee rule and on how your plan works.

If you delay Part B while you have qualifying employer coverage, you get a Special Enrollment Period — up to 8 months after the job or the group coverage ends, whichever comes first — to sign up without a late penalty.

Heads up: COBRA and retiree coverage do not count as active employer coverage for this rule. Once your active job ends, the Part B clock starts, even if COBRA is still paying claims. Missing that window can mean a permanent 10% premium penalty for each 12 months you could have had Part B but didn't.

Where Part D fits in

Part D covers prescription drugs. If your employer plan includes drug coverage that Medicare considers "creditable" (at least as good as standard Part D), you can delay Part D without a penalty. Your plan should send you a notice each year telling you whether your drug coverage is creditable — keep it.

A few Part D facts worth knowing whenever you do enroll:

• The out-of-pocket cap for covered drugs is $2,100 in 2026 and $2,400 in 2027.
• The maximum Part D deductible is $615 in 2026 and $700 in 2027.
• The old coverage gap, or "donut hole," is gone as of 2025.
• The Medicare Prescription Payment Plan lets you spread your drug costs into monthly payments instead of paying big amounts at the pharmacy counter.

A quick note on higher incomes

If your income is above $109,000 as a single filer in 2026 (higher for joint filers), you may pay an income-related surcharge called IRMAA on top of your Part B and Part D premiums. Social Security uses your tax return from two years earlier. If your income has dropped because you retired or cut back hours, you can ask Social Security to reconsider.

What's available around Hartford

Hartford is in Hartford County, where Medicare beneficiaries can choose Original Medicare (with or without a stand-alone Part D drug plan and, if they wish, a Medigap policy) or a Medicare Advantage plan from a range of carriers. The specific plan lineup is updated each fall for the next calendar year — check your plan's ANOC and compare what's offered in your ZIP code at medicare.gov/plan-compare.

Two dates to keep on the fridge:

• Oct. 15 – Dec. 7: Medicare Annual Enrollment Period, when you can join, switch, or drop Advantage and Part D plans.
• Jan. 1 – March 31: Medicare Advantage Open Enrollment, when people already in an Advantage plan can make one change.